Hecogenin
Structural Formula Vector Image
Title: Hecogenin
CAS Registry Number: 467-55-0
CAS Name: (3b,5a,25R)-3-Hydroxyspirostan-12-one
Molecular Formula: C27H42O4
Molecular Weight: 430.62
Percent Composition: C 75.31%, H 9.83%, O 14.86%
Literature References: A steroidal sapogenin which has been isolated from plants, particularly from numerous Agave species. Isoln: Marker et al., J. Am. Chem. Soc. 69, 2167 (1947); Rubin, US 3303186 (1967). Synthesis and configuration: Mazur et al., J. Am. Chem. Soc. 82, 5889 (1960). Separation of an optically inactive product from sapogenin mixtures: Cardenas, US 3013010 (1961 to Searle). Review: L. F. Fieser, M. Fieser, Steroids (Reinhold, New York, 1959) pp 667-671 sqq.
Properties: Crystals from acetone, mp 264-266°. [a]D +8° (CHCl3) (Mazur et al.); mp 245°, 253°, 268° (Marker et al.); mp 240-245°, 245-250°. [a]D ±0° (CHCl3) (Cardenas).
Melting point: mp 264-266°; mp 245°, 253°, 268° (Marker et al.); mp 240-245°, 245-250°
Optical Rotation: [a]D +8° (CHCl3) (Mazur et al.); [a]D ±0° (CHCl3) (Cardenas)
 
Derivative Type: Pseudohecogenin
CAS Registry Number: 11005-20-2
CAS Name: (3b,5a,25R)-3,26-Dihydroxyfurost-20(22)-en-12-one
Molecular Formula: C27H42O4
Molecular Weight: 430.62
Percent Composition: C 75.31%, H 9.83%, O 14.86%
Literature References: Prepn from hecogenin: Cameron et al., J. Chem. Soc. 1955, 2807; Wall, Serota, US 2870143 (1959 to USDA).
Properties: Plates from aq acetone, mp 190-191°. [a]D20 +103° (c = 1.5 in chloroform), +96° (c = 1 in dioxane). uv max (ethanol): 213 nm (e 6400).
Melting point: mp 190-191°
Optical Rotation: [a]D20 +103° (c = 1.5 in chloroform), +96° (c = 1 in dioxane)
Absorption maximum: uv max (ethanol): 213 nm (e 6400)
 
Use: In prepn of steroidal hormones.

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